Model studies on the synthesis of (1R) 1-H3, H2, H1)- octane and (1S) (1-H3, H2, H1) -octane were pursued. It was proved that M. smegmatis converts 1-C14 octane to 1-c14 octanol and 1-C14 octanal. The incubation of (1R) (1-H3, 1-C14) octanol with M. smegmatis gave (1-H3, 1-C14) octanal. This established that the alcohol dehydrogenase of M. smegmatis abstracts the 1-pro S hydrogen of the octanol.